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MilliporeSigma

324515

Sigma-Aldrich

trans-1,4-Dichloro-2-butene

98%

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About This Item

Linear Formula:
ClCH2CH=CHCH2Cl
CAS Number:
110-57-6
Molecular Weight:
125.00
Beilstein/REAXYS Number:
1719693
EC Number:
203-779-7
MDL number:
MFCD00000988
UNSPSC Code:
12352100
PubChem Substance ID:
24859448
NACRES:
NA.22

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vapor pressure

10 mmHg ( 20 °C)

Quality Level

200

assay

98%

form

liquid

refractive index

n20/D 1.488 (lit.)

bp

74-76 °C/40 mmHg (lit.)

mp

1-3 °C (lit.)

density

1.183 g/mL at 25 °C (lit.)

functional group

chloro

storage temp.

2-8°C

SMILES string

ClC\C=C\CCl

InChI

1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+

InChI key

FQDIANVAWVHZIR-OWOJBTEDSA-N

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1 of 4

This Item
215082D39207593028
trans-1,4-Dichloro-2-butene 98%

Sigma-Aldrich

324515

trans-1,4-Dichloro-2-butene

trans-1,4-Dichloro-2-butene technical grade, 85%, remainder predominantly cis isomer

Sigma-Aldrich

215082

trans-1,4-Dichloro-2-butene

trans-1,4-Dibromo-2-butene 99%

Sigma-Aldrich

D39207

trans-1,4-Dibromo-2-butene

trans-4-Octene 98%

Sigma-Aldrich

593028

trans-4-Octene

assay

98%

assay

85%

assay

99%

assay

98%

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

bp

74-76 °C/40 mmHg (lit.)

bp

74-76 °C/40 mmHg (lit.)

bp

205 °C (lit.)

bp

122-123 °C (lit.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

mp

1-3 °C (lit.)

mp

1-3 °C (lit.)

mp

48-51 °C (lit.)

mp

-

form

liquid

form

liquid

form

crystals

form

-

Application

trans-1,4-Dichloro-2-butene may be used for the alkylation of adenine to 9-alkylpurines.[1] It can react with diethyl malonate to form vinylcyclopropane derivative.[2] It can also undergo asymmetric allylic alkylation with Grignard reagents in the presence of copper thiophene carboxylate catalyst.[3]

Other Notes

85%, remainder predominantly cis isomer

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

127.4 °F - closed cup

flash_point_c

53 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF1002
MKBZ5026V
MKBZ5024V
MKBZ5021V
MKBZ5027V

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High Diversity on Simple Substrates: 1, 4?Dihalo?2?butenes and Other Difunctionalized Allylic Halides for Copper?Catalyzed SN2? Reactions.
Falciola C A, et al.
Chemistry?A European Journal , 14(34), 10615-10627 (2008)
Improved selectivity in the preparation of some 1, 1-difunctionalized 3-cyclopentenes. High yield synthesis of 3-cyclopentenecarboxylic acid.
Depres JP and Greene AE.
The Journal of Organic Chemistry, 49(5), 928-931 (1984)
S Phadtare et al.
Journal of medicinal chemistry, 30(2), 437-440 (1987-02-01)
Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1,4-dichloro-2-butene (4), effected by K2CO3 in dimethyl sulfoxide or tetra-n-butylammonium fluoride in tetrahydrofuran, led in 90-95% regioselectivity to 9-alkylpurines 6a and 6b. The title compounds 2a and 2b were obtained by
S Phadtare et al.
Nucleic acids symposium series, (18)(18), 25-28 (1987-01-01)
Reaction of adenine (1a) or cytosine (1b) with excess 1,4-dichloro-2-butyne catalyzed by K2CO3 in (CH3)2SO gave the 4-chloro-2-butynyl derivatives 2a and 2b. The latter were converted to the 4-hydroxy-2-butynyl compounds 3a and 3b by refluxing in 0.1 M HCl. Isomerization
L S Mullin et al.
Drug and chemical toxicology, 23(3), 403-417 (2000-08-26)
This study was conducted to elucidate the time- and dose-response relationships of long-term, low-level 1,4-dichlorobutene-2 (DCB) inhalation exposure to nasal tumor induction in rats. Male Crl:CD BR rats were exposed 6 hours per day, 5 days week to 0, 0.1
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